Triethylamine → HCID 59472138, 화합물

HRID 78666

반응식

HRID 78666 반응식
[NH:1]([C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:7][CH:6]=1)=[O:4])[NH2:2].[NH2:21][C:22]1[C:27]([C:28](O)=[O:29])=C[C:25]([Br:31])=[CH:24][N:23]=1.C([N:34](CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C.O>[NH2:21][C:22]1[C:27]([C:28]([NH:2][NH:1][C:3]([C:5]2[CH:6]=[CH:7][C:8]([CH2:11][N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[CH:9][CH:10]=2)=[O:4])=[O:29])=[N:34][C:25]([Br:31])=[CH:24][N:23]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 7374452-Amino-5-bromonicotinic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67425410tert-butyl N-[[4-(hydrazinecarbonyl)phenyl]methyl]-N-methyl-carbamate

생성물 1

HCID 59472138HCID 59472138, 화합물수율 99.7%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of tert-butyl N-[[4-(hydrazinecarbonyl)phenyl]methyl]-N-methyl-carbamate (1 g, 3.580 mmol) in DMF (7.769 mL) and 2-amino-5-bromo-pyridine-3-carboxylic acid (776.9 mg, 3.580 mmol) was added triethylamine (724.5 mg, 997.9 μL, 7.160 mmol) followed by TBTU (1.724 g, 5.370 mmol). The resulting mixture was stirred at room temperature for 48 h. The reaction mixture was diluted with ethyl acetate (20 mL) and water (20 mL) and the layers separated. The aqueous layer was extracted further with ethyl acetate (2×20 mL) and combined organic extracts washed with saturated aqueous sodium hydrogen carbonate solution (1×20 mL), brine (1×20 mL), dried over MgSO4 and concentrated in vacuo. The residue was triturated with CH2Cl2 to give the product as a white solid (1.71 g, 58% yield); 1H NMR (400.0 MHz, DMSO) d 1.39-1.45 (m, 9H), 2.80 (s, 3H), 4.45 (s, 2H), 4.45 (s, 2H), 7.28 (s, 2H), 7.35 (d, 2H), 7.90 (d, 2H), 8.20 (d, 2H), 8.24 (d, 1H), 10.50 (s, 1H) and 10.54 (s, 1H) ppm; MS (ES+) 480.16

후처리

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted further with ethyl acetate (2×20 mL)
  3. washcombined organic extracts washed with saturated aqueous sodium hydrogen carbonate solution (1×20 mL), brine (1×20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with CH2Cl2

출처 및 근거

ORD 기록
ord-27688f8e8afa4aafbfee32e7527ab68b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841308B2

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